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A mutagenic anthraquinone, lucidin (1), occurring in Rubiaceae plants, reacted with nucleic bases under physiological conditions to form adducts. The order of the reactivity is as follows: adenine &gt; guanine &gt;&gt; pyrimidine bases approximately 0. By spectroscopic analyses, the isolated purine base adducts were identified as condensed reactants at the benzylic position of 1 with a nitrogen atom of a purine base. The results indicate a strong possibility of the formation of an exomethylenic compound as an electrophile intermediate.

chemical and pharmaceutical bulletin/chemical and pharmaceutical bulletin

Identification of Adducts Formed by Reaction of Purine Bases with a Mutagenic Anthraquinone, Lucidin: Mechanism of Mutagenicity by Anthraquinones Occurring in Rubiaceae Plants.